Rh(II)‐Catalyzed Tandem Reaction of 2‐Trimethylsiloxy‐pyridine and α‐Trifluoromethyl Diazomethane: An Approach to Tetrasubstituted gem‐Difluoro Olefins

Herein, we describe a Rh2(OAc)4‐catalyzed reaction of 2‐trimethylsiloxy‐pyridine and fluorinated diazomethanes, which provides an effective and straightforward approach to the synthesis of 2‐oxopyridinyl tetrasubstituted gem‐difluoro olefins. This protocol features good functional group compatibilit...

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Published in:European journal of organic chemistry 2024-12, Vol.27 (48), p.n/a
Main Authors: Li, Guang‐Hui, Huang, Xin‐Yu, Lv, Jun‐Xi, Zhao, Xue‐Di, Yang, Shengchao, Liu, Lu
Format: Article
Language:English
Subjects:
2-oxopyridinyl
2-trimethylsiloxy-pyridine
Alkenes
Cascade chemical reactions
Chemical synthesis
Diazomethane
Functional groups
gem-difluoro olefin
Pyridines
rhodium-catalyzed
trifluoromethyl carbene
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Huang, Xin‐Yu
Lv, Jun‐Xi
Zhao, Xue‐Di
Yang, Shengchao
Liu, Lu
description Herein, we describe a Rh2(OAc)4‐catalyzed reaction of 2‐trimethylsiloxy‐pyridine and fluorinated diazomethanes, which provides an effective and straightforward approach to the synthesis of 2‐oxopyridinyl tetrasubstituted gem‐difluoro olefins. This protocol features good functional group compatibility, mild reaction conditions, good yield, and readily available substrates. A tandem Rhodium‐catalyzed tandem ylide formation/1,5‐elimination reactions of 2‐trimethylsiloxy‐pyridine and α‐trifluoromethyl diazomethane is disclosed for the first time, which reveals a novel tool for the synthesis of 2‐oxopyridinyl tetrasubstituted gem‐difluoroalkenes.
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A tandem Rhodium‐catalyzed tandem ylide formation/1,5‐elimination reactions of 2‐trimethylsiloxy‐pyridine and α‐trifluoromethyl diazomethane is disclosed for the first time, which reveals a novel tool for the synthesis of 2‐oxopyridinyl tetrasubstituted gem‐difluoroalkenes.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202400899</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>2-oxopyridinyl ; 2-trimethylsiloxy-pyridine ; Alkenes ; Cascade chemical reactions ; Chemical synthesis ; Diazomethane ; Functional groups ; gem-difluoro olefin ; Pyridines ; rhodium-catalyzed ; trifluoromethyl carbene</subject><ispartof>European journal of organic chemistry, 2024-12, Vol.27 (48), p.n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0003-2151-891X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Li, Guang‐Hui</creatorcontrib><creatorcontrib>Huang, Xin‐Yu</creatorcontrib><creatorcontrib>Lv, Jun‐Xi</creatorcontrib><creatorcontrib>Zhao, Xue‐Di</creatorcontrib><creatorcontrib>Yang, Shengchao</creatorcontrib><creatorcontrib>Liu, Lu</creatorcontrib><title>Rh(II)‐Catalyzed Tandem Reaction of 2‐Trimethylsiloxy‐pyridine and α‐Trifluoromethyl Diazomethane: An Approach to Tetrasubstituted gem‐Difluoro Olefins</title><title>European journal of organic chemistry</title><description>Herein, we describe a Rh2(OAc)4‐catalyzed reaction of 2‐trimethylsiloxy‐pyridine and fluorinated diazomethanes, which provides an effective and straightforward approach to the synthesis of 2‐oxopyridinyl tetrasubstituted gem‐difluoro olefins. 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subjects 2-oxopyridinyl
2-trimethylsiloxy-pyridine
Alkenes
Cascade chemical reactions
Chemical synthesis
Diazomethane
Functional groups
gem-difluoro olefin
Pyridines
rhodium-catalyzed
trifluoromethyl carbene
title Rh(II)‐Catalyzed Tandem Reaction of 2‐Trimethylsiloxy‐pyridine and α‐Trifluoromethyl Diazomethane: An Approach to Tetrasubstituted gem‐Difluoro Olefins
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